RU2016136430A - Parenteral compositions of celecoxib - Google Patents

Parenteral compositions of celecoxib Download PDF

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RU2016136430A
RU2016136430A RU2016136430A RU2016136430A RU2016136430A RU 2016136430 A RU2016136430 A RU 2016136430A RU 2016136430 A RU2016136430 A RU 2016136430A RU 2016136430 A RU2016136430 A RU 2016136430A RU 2016136430 A RU2016136430 A RU 2016136430A
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emulsion
celecoxib
less
amount
oil
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RU2016136430A
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RU2016136430A3 (en
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Франклин ОКУМУ
Жан-Жон ЧУ
Жюли Энн ВЕБ
Рафаэль Энтони САБИНО
Эндрю Сянь Чэнь
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Др. Редди'С Лабораторис Лтд.
Франклин ОКУМУ
Жан-Жон ЧУ
Жюли Энн ВЕБ
Рафаэль Энтони САБИНО
Эндрю Сянь Чэнь
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers

Claims (20)

1. Эмульсия целекоксиба масло-в-воде, включающая целекоксиб, дисперсную фазу, включающую масло, лецитин, и водную дисперсионную фазу; причем целекоксиб растворен в эмульсии и присутствует в количестве примерно 0,6%, мас./мас., эмульсии или меньше; и при этом массовое отношение целекоксиба к лецитину составляет примерно 0,1:1 или меньше.1. An emulsion of celecoxib oil-in-water, including celecoxib, a dispersed phase comprising oil, lecithin, and an aqueous dispersion phase; moreover, celecoxib is dissolved in the emulsion and is present in an amount of about 0.6%, w / w, emulsion or less; and the mass ratio of celecoxib to lecithin is about 0.1: 1 or less. 2. Эмульсия по п. 1, которая включает, по меньшей мере, один параметр из следующих: общее количество масла составляет примерно 6%, мас./мас., эмульсии или меньше; суммарное количество масла и лецитина составляет примерно 12%, мас./мас., эмульсии или меньше; эмульсия имеет вязкость примерно 1 сП - примерно 1000 сП; или эмульсию можно фильтровать через фильтр 0,2 микрона.2. The emulsion according to claim 1, which includes at least one parameter of the following: the total amount of oil is about 6%, w / w, emulsion or less; the total amount of oil and lecithin is about 12%, w / w, emulsion or less; the emulsion has a viscosity of about 1 cP - about 1000 cP; or the emulsion can be filtered through a 0.2 micron filter. 3. Эмульсия по п. 1, в которой рН колеблется от примерно 4 до примерно 9.3. The emulsion according to claim 1, in which the pH ranges from about 4 to about 9. 4. Эмульсия по п. 1, в которой дисперсная фаза включает среднецепной триглицерид, растительное масло или их смесь.4. The emulsion according to claim 1, in which the dispersed phase comprises a medium chain triglyceride, vegetable oil, or a mixture thereof. 5. Эмульсия по п. 1, в которой лецитин выбирают из соевого лецитина, яичного лецитина или их смеси.5. The emulsion according to claim 1, wherein the lecithin is selected from soya lecithin, egg lecithin, or a mixture thereof. 6. Эмульсия по п. 1, дополнительно включающая хелатообразователь, выбранный из ЭДТК или гистидина.6. The emulsion according to claim 1, further comprising a chelating agent selected from EDTA or histidine. 7. Эмульсия по п. 1, дополнительно включающая тонический агент, выбранный из сахарозы или глицерина.7. The emulsion according to claim 1, further comprising a tonic agent selected from sucrose or glycerol. 8. Эмульсия по п. 1, в которой средний размер капель дисперсной фазы составляет примерно 200 нанометров или меньше.8. The emulsion according to claim 1, in which the average droplet size of the dispersed phase is about 200 nanometers or less. 9. Эмульсия по п. 1, которую можно инъецировать.9. The emulsion according to claim 1, which can be injected. 10. Способ лечения боли у пациента, нуждающегося в этом, включающий парентеральное введение за период примерно 15 - примерно 45 минут пациенту, нуждающемуся в этом, количества эмульсионной композиции целекоксиба, достаточного для лечения такой боли, причем композиция включает целекоксиб, дисперсную фазу, включающую масло, лецитин, и водную дисперсионную фазу; причем целекоксиб присутствует в количестве примерно 0,6%, мас./мас., эмульсии или меньше; массовое отношение целекоксиба к лецитину составляет примерно 0,1:1 или меньше, и при этом эмульсия включает, по меньшей мере, один параметр из следующих: общее количество масла составляет примерно 6%, мас./мас., или меньше; суммарное количество масла и лецитина составляет примерно 12%, мас./мас., или меньше; эмульсия имеет вязкость от примерно 1 сП до примерно 1000 сП; или эмульсию можно фильтровать через фильтр 0,2 микрона.10. A method of treating pain in a patient in need thereof, comprising parenteral administration for a period of about 15 to about 45 minutes to a patient in need thereof, of an amount of celecoxib emulsion composition sufficient to treat such pain, the composition comprising celecoxib, a dispersed phase comprising oil , lecithin, and an aqueous dispersion phase; moreover, celecoxib is present in an amount of about 0.6%, w / w, emulsion or less; the mass ratio of celecoxib to lecithin is about 0.1: 1 or less, and the emulsion includes at least one of the following: the total amount of oil is about 6%, w / w, or less; the total amount of oil and lecithin is about 12%, w / w, or less; the emulsion has a viscosity of from about 1 cP to about 1000 cP; or the emulsion can be filtered through a 0.2 micron filter. 11. Способ по п. 10, в котором количество целекоксиба, вводимое в одноразовой парентеральной дозе, колеблется от примерно 50 мг до примерно 800 мг.11. The method of claim 10, wherein the amount of celecoxib administered in a single parenteral dose ranges from about 50 mg to about 800 mg. 12. Способ по п. 10, в котором за введением необязательно следует, по меньшей мере, одно следующее парентеральное введение эмульсионной композиции целекоксиба, включающей целекоксиб в количестве от примерно 50 мг до примерно 800 мг.12. The method according to p. 10, in which the introduction is optionally followed by at least one subsequent parenteral administration of an emulsion composition of celecoxib, comprising celecoxib in an amount of from about 50 mg to about 800 mg. 13. Способ по п. 12, в котором несколько парентеральных введений осуществляют с интервалом каждые 2 часа (2q), каждые 4 часа (4q), каждые 6 часов (6q), каждые 8 часов (8q), каждые 10 часов (10q) или каждые 12 часов (12q), или как определяет лечащий врач.13. The method according to p. 12, in which several parenteral administration is carried out at intervals of every 2 hours (2q), every 4 hours (4q), every 6 hours (6q), every 8 hours (8q), every 10 hours (10q) or every 12 hours (12q), or as determined by the attending physician. 14. Способ уменьшения боли у человека, нуждающегося в этом, включающий введение пациенту, по меньшей мере, одной парентеральной дозы наноэмульсионной композиции масло-в-воде, включающей целекоксиб в концентрации от примерно 0,5 мг/мл до примерно 20 мг/мл и в количестве от примерно 50 мг до примерно 800 мг, за период времени от примерно 15 минут до примерно 45 минут, причем средний диаметр капель наноэмульсии составляет примерно 200 нанометров или меньше, и при этом целекоксиб растворен в эмульсии.14. A method of reducing pain in a person in need thereof, comprising administering to the patient at least one parenteral dose of an oil-in-water nanoemulsion composition comprising celecoxib in a concentration of from about 0.5 mg / ml to about 20 mg / ml, and in an amount of from about 50 mg to about 800 mg, over a period of time from about 15 minutes to about 45 minutes, wherein the average diameter of the nanoemulsion droplets is about 200 nanometers or less, and celecoxib is dissolved in the emulsion. 15. Способ по п. 10 или 14, в котором композиция целекоксиба обеспечивает, по меньшей мере, один из следующих фармакокинетических параметров: средняя максимальная концентрация в плазме (Cmax) от примерно 750 нг/мл до примерно 20300 нг/мл; AUC(0-12) от примерно 1400 час*нг/мл до примерно 55300 час*нг/мл; AUClast от примерно 1300 час*нг/мл до примерно 55300 час*нг/мл; или AUC(0-inf) от примерно 14000 час*нг/мл до примерно 55,300 час*нг/мл; общий кажущийся объем распределения (Vss) от примерно 100 л до примерно 180 л; или общий кажущийся объем распределения (Vss) указанного введения наноэмульсионной композиции составляет меньше 50 процентов по сравнению с общим кажущимся объемом распределения (Vss) целебрекса® 200 MG или целебрекса® 400 MG.15. The method according to p. 10 or 14, in which the celecoxib composition provides at least one of the following pharmacokinetic parameters: average maximum plasma concentration (C max ) from about 750 ng / ml to about 20300 ng / ml; AUC (0-12) from about 1400 hours * ng / ml to about 55300 hours * ng / ml; AUC last from about 1300 hour * ng / ml to about 55300 hour * ng / ml; or AUC (0-inf) from about 14,000 hours * ng / ml to about 55,300 hours * ng / ml; total apparent distribution volume (V ss ) from about 100 L to about 180 L; or the total apparent volume of distribution (V ss ) of said administration of the nanoemulsion composition is less than 50 percent compared with the total apparent volume of distribution (V ss ) of celebrex® 200 MG or celebrex® 400 MG. 16. Способ по п. 10 или 14, в котором композиция обеспечивает среднюю максимальную концентрацию в плазме (Cmax), по меньшей мере, 3-кратную от концентрации Cmax, являющейся результатом перорального введения эквивалентного количества целекоксиба.16. The method of claim 10 or 14, wherein the composition provides an average maximum plasma concentration (C max ) of at least 3 times that of C max resulting from the oral administration of an equivalent amount of celecoxib. 17. Эмульсия по п. 1, которая включает целекоксиб в количестве от примерно 0,005 до примерно 1,0%, мас./мас., композиции, дисперсную фазу, отвечающую за от примерно 5% до примерно 50%, мас./мас., композиции, дисперсионную водную среду в количестве от примерно 50%, мас./мас., до примерно 95%, мас./мас., композиции; и эмульгатор в количестве от примерно 0,01% до примерно 20%, мас./мас., композиции, причем дисперсная фаза имеет капли со средним диаметром менее 200 нм, и при этом целекоксиб растворен в эмульсии.17. The emulsion according to claim 1, which includes celecoxib in an amount of from about 0.005 to about 1.0%, wt./wt., Composition, dispersed phase, responsible for from about 5% to about 50%, wt./wt. , compositions, dispersion aqueous medium in an amount of from about 50% w / w to about 95% w / w composition; and an emulsifier in an amount of from about 0.01% to about 20%, w / w, of the composition, the dispersed phase having droplets with an average diameter of less than 200 nm, while celecoxib is dissolved in the emulsion. 18. Наноэмульсия целекоксиба по п. 17 имеет, по меньшей мере, одну из следующих характеристик: величина PFAT меньше 0,05%; вязкость от примерно 1 сП до примерно 3 сП; величина рН от примерно 3 до примерно 9; индекс полидисперсности примерно менее 0,8; пропускание более примерно 10%; зета-потенциал в интервале от -50 мВ до +50 мВ; D50 среднего диаметра капель меньше 200 нм при измерении при 2-8 градусах С; 25 градусах С/60% RH и 30 градусах С, 6 месяцев; или как D50, так и D90 среднего диаметра капель меньше 250 нм при измерении при 30 градусах С, 6 месяцев.18. Celecoxib nanoemulsion according to claim 17 has at least one of the following characteristics: PFAT value less than 0.05%; viscosity from about 1 cP to about 3 cP; a pH of from about 3 to about 9; a polydispersity index of less than about 0.8; transmittance of more than about 10%; zeta potential in the range from -50 mV to +50 mV; D50 average droplet diameter less than 200 nm when measured at 2-8 degrees C; 25 degrees C / 60% RH and 30 degrees C, 6 months; or both D50 and D90 of the average droplet diameter are less than 250 nm when measured at 30 degrees C, 6 months. 19. Способ получения наноэмульсионной композиции целекоксиба для парентерального введения, включающий предоставление целекоксиба, эмульгатора, масла, воды, причем количество эмульгатора равно или больше количества масла, количество воды составляет от примерно 85 до примерно 95%, мас./мас., и количество целекоксиба составляет от примерно 0,005 до примерно 0,5%, мас./мас.; и микрофлюидизацию при рН, колеблющемся от примерно 7,5 до примерно 9,0 и давлении от примерно 69000 до примерно 207000 кПа (10000-30000 ф/д2); причем посредством этого получают наноэмульсию, в которой средний диаметр капель составляет менее примерно 200 нм.19. A method of obtaining a nanoemulsion composition of celecoxib for parenteral administration, comprising providing celecoxib, emulsifier, oil, water, wherein the amount of emulsifier is equal to or greater than the amount of oil, the amount of water is from about 85 to about 95%, w / w, and the amount of celecoxib is from about 0.005 to about 0.5%, w / w; and microfluidization at a pH ranging from about 7.5 to about 9.0 and a pressure of from about 69000 to about 207000 kPa (10,000-30,000 lb / d 2); whereby a nanoemulsion is obtained in which the average droplet diameter is less than about 200 nm. 20. Способ по п. 19, дополнительно включающий образование грубой эмульсии перед микрофлюидизацией, причем грубая эмульсия имеет диаметр капель более 200 нм и до примерно 800 нм, и причем образование грубой эмульсии происходит при рН, который выше рН, используемого при микрофлюидизации.20. The method according to p. 19, further comprising the formation of a coarse emulsion before microfluidization, and the coarse emulsion has a droplet diameter of more than 200 nm and up to about 800 nm, and moreover, the formation of a coarse emulsion occurs at a pH that is higher than the pH used in microfluidization.
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JP2017505349A (en) 2017-02-16
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AU2015217309A1 (en) 2016-08-25
CA2939562A1 (en) 2015-08-20
CN108472253A (en) 2018-08-31
EP3104840B1 (en) 2019-05-29
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US9446056B2 (en) 2016-09-20
EP3104840A1 (en) 2016-12-21

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